The compound 1232zd is a known compound. This compound is one kind of hydrofluoroolefin (HFO) with a low global warming potential coefficient (GWP) and has been expected as an operation medium for a thermal cycle.
As a manufacturing method of 1232zd, a method is known where 1,1,3,3,3-pentachloropropane (hereinafter, also referred to as 240fa) is fluorinated in a gas phase in the presence of hydrogen fluoride, for example (Japanese Patent Application Publication No. 2012-20992). A method is also known where 1,1,3,3-tetrachloropropene (hereinafter, also referred to as 1230za) is chlorofluorinated with chlorine and hydrogen fluoride in a gas phase (Japanese Patent Application Publication No. H10-309464). Although 1232zd can be obtained in a high yield by each method, use of a more than stoichiometric amount of hydrogen fluoride is required. The use of a large amount of hydrogen fluoride increases the risk of an accident resulting in injury or death and puts pressure on risk management when leaked.
An industrially applicable manufacturing method for manufacturing 1232zd is still being demanded.